


Experimenting

by bestGuesses



Category: Supernatural
Genre: Anal, Anal Fingering, Anal Sex, BDSM, Barebacking, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Cock Rings, Demon Dean Winchester, Established Castiel/Dean Winchester, Friends With Benefits, Gags, Gay, Gay Sex, Hand Jobs, M/M, Orgasm Delay, Orgasm Delay/Denial, Safewords, Smut, Top Dean Winchester, probably the only bottom!cas ill ever write
Language: English
Status: Completed
Published: 2019-08-24
Updated: 2019-08-24
Packaged: 2020-09-25 06:15:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,336
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20372026
Author URL: https://archiveofourown.org/users/bestGuesses/pseuds/bestGuesses
Summary: When Dean became a demon, he decided to do a bit more sexual exploration. Cas is really just along for the ride.





	Experimenting

**Author's Note:**

> first of all, im just finishing all of my drafts, so this is probably gonna be the last one for a minute! this was actually written in the midst of terrible writer's block so please bare with me, i really just wanted to challenge myself since i am very heavily a bottom!dean fan lmao  
second of all, i dont think im going to be writing much (if any) bottom!cas besides this. id move my wattpad fics over if i had any confidence in them. anyway, enjoy and prepare yourself for the next onslaught of fics, i have a lot planned

Cas wasn’t sure when their fling started. His guess was a few years back, but there was no official time where they went beyond friends. What started out as glares across the room turned into the occasional passing smile. Smiles turned into nudges, nudges into kissing, and kissing into much,  _ much _ more.

Cas really loved it.

He would never admit it, but he knew damn well he craved the attention as much as Dean. He loved the way Dean sobbed into the mattress as he fucked him hard. The way Dean would clutch desperately onto his hips as he tried to deepthroat. Cas adored it, along with every new thing they had tried. 

Needless to say, when Dean became a demon, Cas was definitely hesitant. He knew that it was still  _ Dean _ , just a very corrupted version of him. And yeah, he definitely couldn’t hold back when Dean was desperately grinding against him and whispering filthy things into his ear. Soon enough, their normal schedule of fucking like rabbits whenever they got the chance returned. Demon Dean was much more adventurous and liked to try new things constantly.

Cas knew he was just along for the ride.

Every new kink Dean tried, he loved. Cas definitely drew a few lines but found that most things were just as good for him as they were for Dean. That didn’t change how Cas choked when he heard Dean’s latest suggestion.

“You should bottom tonight,” Dean said simply. He was smirking a bit from where he was sitting on their bed.

Cas looked up from the book he was reading. He sat up a bit straighter from where he was perched on the couch, “Dean, no offense, but if I tap you hard enough you beg.”

Dean rolled his eyes. “I happen to have more self-control than you think, Castiel.”

Cas weighed his options. He hadn’t bottomed in a  _ long _ time, and he almost certainly had never submitted sexually. But it wouldn’t be such an absurd idea to at least try. So eventually, Cas found himself kneeling on the bed. His arms were tied securely behind his back with his signature blue tie, a ball gag in his mouth and a cock ring on. He glared at Dean. They had a mutual knowledge that Cas wouldn’t go down without a fight.

“Look at my angel, all pretty and tied up,” Dean said with a low chuckle, cupping his jaw with his hand as his eyes flickered black. Cas huffed, a bit red in the face. Dean moved over, grabbing his ass and beginning to prep him with some demonic magic.

Dean pulled Cas in close to leave a few hickeys on his neck before reaching a finger over the rim of Cas’ hole, pushing in. Cas made a low whining noise, leaning against Dean. From the way it took him a moment to adjust to the feeling, it was clear he wasn’t used to being fingered. Even when it started to feel good, Cas refused to sink back onto Dean’s hand. Dean chuckled at that.

  
“Still resisting, babe?” He asked with a grin. Cas glared as Dean pushed another finger inside. He knew Dean had prepped him and was only really teasing him as he searched for his prostate. As soon as he found it, he slammed his fingers against the bundle of nerves, watching as Cas tensed up with a muffled moan. He fought against the restraint on his wrists, not wanting to show how much he loved it, how much of a slut he was for Dean’s fingers in him… it was a losing battle.

“We should do this more often,” Dean said before slipping a third finger in Cas. He fucked him for a while with his fingers only, watching as Cas continued trying to resist. Pretty little gasps were falling from his lips with every press of Dean’s fingers. It was clear that Cas was enjoying it, although Dean knew he’d never openly admit it. Just to be safe, however, he decided to give Cas the option to opt-out.

“If you want me to stop, drop this,” Dean said, handing him a lube bottle. “It works as a safe word.” Cas nodded, gripping it tightly as Dean smirked. He unzipped his pants, palming his hard cock through his underwear. Cas looked on enviously, his own leaking cock receiving no attention. 

Dean laughed at his expression. “You won’t be needing to touch yourself, angel,” he promised before slowly pulling his pants off entirely. His underwear followed soon after. He then laid down, grabbing Cas by the waist, his hands firm on Cas’ bare skin as he moved him. Soon enough, Cas was facing Dean and in just about the right position to sink down on his cock. Cas’ thighs were almost trembling as he continued his effort to hide how turned on he was, still holding the lube bottle to signify that he was still all good. Dean snapped his fingers, slicking himself up without even touching himself before positioning the blunt head of his cock against Cas’ rim.

“You ready?” He asked. Dean waited for Cas’ nod before lowering himself, letting out a whine as he bottomed out.

“ _ Fuck _ ,” Dean gasped as Cas sat there for a moment, ducking his head as he got used to the feeling. Cas took a few deep breaths, biting down on his gag as he waited for the slight stretching burn to subside.

“Go ahead and move, baby,” Dean cooed, cupping Cas’ jaw and forcing him to make eye contact. Cas slowly lifted himself before sinking back down, shutting his eyes tightly. He tried to fight the gag, his eyes glowing blue as he attempted to use his grace to get it out of his mouth. Dean flickered his own eyes black in warning and Cas huffed, the glow persisting as he repeatedly lifted and dropped himself on Dean’s cock. He picked up the pace, adjusting his angle a few times before letting out a muffled moan, clearly hitting his prostate. He slowly opened his eyes, looking right at Dean as he continued riding him hard.

“Look at you, angel,” Dean chuckled with a few whimpers whenever Cas made any sudden movements, “Finally bottoming. Feel good?” He asked. Cas glared as Dean bucked his hips up, his grumpy expression cut off audibly gasped, the proceeding moan mostly muffled. Dean laughed at that, fucking up into Cas and watching him come apart, still trying to break free of his bonds. The glow of his eyes only got stronger as Dean laughed. He moved Cas off of him, managing to position him comfortably on his knees before placing his hands firmly on his hips and fucking him hard. Cas gave a few strangled moans, ducking his head forward as Dean supported him.

“Wanna cum?” Dean asked. Cas nodded profusely.

“Too bad,” He laughed. Cas whimpered as Dean only sped up, Cas managing to spread his legs out of pure instinct. Soon enough, he was reaching his own climax, gripping Cas’ sides tightly and fucking into him hard. It wasn’t long until he was filling Cas up, who gave a moan in response, clearly desperate to finish. Dean chuckled, taking pity on him and pulling out before flipping him over. He took the gag off as Cas panted.

“Is this some sort of punishment?” Cas asked as Dean pushed two fingers into his hole. He threw his head back as his leg twitched, “ _ Fuck! _ ” He exclaimed before beginning to mumble in Enochian as Dean fucked him with his fingers. After a few minutes, Dean took the cock ring off of him, catching him in a kiss as he fingered him and used his free hand to stroke his cock, watching as Cas quickly unraveled with a scream. He pulled his fingers out, wiping them on the bed sheet before untying him.

“Was that good?” Dean asked.

“I still prefer to top,” Cas replied, panting, “But I’m not opposed to doing this again.”


End file.
